Practical Asymmetric Synthesis of 1,2-Diamines in the 3-Aminoazepane Series

S. Cutri , A. Chiaroni (1) , M. Bonin (2) , L. Micouin (3) , H.-P. Husson

1 ICSN - Institut de Chimie des Substances Naturelles
2 Cirad-TERA - Département Territoires, Environnement et Acteurs
3 SSMIP - Synthèse et structure de molécules d'interet pharmacologique

A simple and versatile method for the enantio-and diastereoselective synthesis of mono-or disubstituted 3-aminoazepanes is described. The key step involves a highly regio-and diastereoselective tandem ring-enlargement/alkylation or reduction process. This novel synthetic route provides enantiomerically pure constrained diamines interesting as scaffolds for medicinal chemistry.

Domaines: Chimie organique

S. Cutri, A. Chiaroni, M. Bonin, L. Micouin, H.-P. Husson. Practical Asymmetric Synthesis of 1,2-Diamines in the 3-Aminoazepane Series. Journal of Organic Chemistry, 2003, 68 (7), pp.2645-2651. ⟨10.1021/jo026711s⟩. ⟨hal-02186903⟩